Tetrahydrofuran → HCID 11118115, compound

HRID 1700500Notes

Reaction equation

HRID 1700500 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][C:11](=O)[CH2:10][C:9](=[O:14])[CH2:8]1.Cl.[NH2:16][CH2:17][C:18]#[C:19][CH3:20].O1CCCC1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(N(CC)CC)C.C(O)C>[CH3:20][C:19]1[C:10]2[C:9](=[O:14])[CH2:8][CH:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:12][C:11]=2[N:16]=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 104651045-pyridin-2-ylcyclohexane-1,3-dioneHCID 12599999But-2-yn-1-amine hydrochloride

Product 1

HCID 11118115HCID 11118115, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-(2-pyridyl)cyclohexane-1,3-dione (2.0 g), 1-amino-2-butyne hydrochloride (0.1.1 g), molecular sieves 4A (2 g), tetrahydrofuran (30 ml) and ethanol (10 ml) was added triethylamine (2.1 g), and the mixture was stirred at room temperature for 1 hour, refluxed for 4 hours and cooled. Insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (EtOAc/MeOH) to give solid. The solid was stirred for 10 hours at 220° C., to which were added ethyl acetate and sodium hydrogen carbonate solution. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give oil of 4-methyl-7-(2-pyridyl)-5,6,7,8-tetrahydroquinolin-5-one (0.28 g).

Workup

  1. temperaturerefluxed for 4 hours
  2. temperaturecooled
  3. filtrationInsoluble materials were filtered off
  4. customUnder reduced pressure, the solvent was evaporated
  5. customthe residue was purified with silica gel column chromatography (EtOAc/MeOH)
  6. customto give solid
  7. stirringThe solid was stirred for 10 hours at 220° C., to which
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-e3ce4006dd664a99925086a4e779d194
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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